Organic Letters 2012-08-17

Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol.

Noelia Araújo, Sarah F Jenkinson, R Fernando Martínez, Andreas F G Glawar, Mark R Wormald, Terry D Butters, Shinpei Nakagawa, Isao Adachi, Atsushi Kato, Akihide Yoshihara, Kazuya Akimitsu, Ken Izumori, George W J Fleet

Index: Org. Lett. 14(16) , 4174-7, (2012)

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Abstract

Ring closure of a 3,5-di-O-triflate derived from D-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.